


Sail Along Silvery Moon

by bourgeois



Category: Supernatural
Genre: 1950s Household Kink, Barebacking, Crossdressing, Light D/s, M/M, Panty Kink
Language: English
Status: Completed
Published: 2014-02-11
Updated: 2014-02-11
Packaged: 2018-01-11 22:12:59
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 7,629
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1178562
Author URL: https://archiveofourown.org/users/bourgeois/pseuds/bourgeois
Summary: <blockquote class="userstuff">
              <p>
  <i>Dean knows he’s rambling, but his heart is doing double time in his chest and he’s pretty sure the words ‘I’m a big sissy freak who thinks about necking his little brother while wearing dresses’ are spelled out in block letters all over his face.</i>
</p><p>written for the <a href="spnkink-meme.livejournal.com">spnkink_meme</a></p>
            </blockquote>





	Sail Along Silvery Moon

“Oh, honey! You’re home!”

It takes all of Dean’s willpower to suppress a bark of laughter as Sam turns around and balks. He flashes a wide grin and does a little twirl, almost losing his footing on the slick floor through lack of finesse. Sam’s still staring at him like he’s grown two heads, and Dean’s already running out of material to keep this joke going until Sam gives him a damn reaction.

If Sam ruins this joke for him, he swears to God the next one will involve whipped cream in his girly shampoo. When Dean found this old time-y skirt and top in one of the many closets of the bunker, tucked deep inside a dusty old box like a secret, the only thought in his head had been “How can I use this to torment my little brother?”. He’d gleefully donned the whole thing (skipping the stockings because, uh, _hello_?) and rushed to the living area where Sam had his face glued to his laptop screen.

Now that he’s actually standing in front of Sam, uncertainty begins to creep up his spine. Awkwardly, he clears his throat and cocks his hip dramatically to the side in an attempt to salvage the humor of the situation. “Get it? Because I do all the goddamn work around here? When’s the last time you washed the dishes, dude?”

The shocked look on Sam’s face doesn’t let up and Dean’s smile finally falls off his face. The full reality of the situation sort of hits him then, what exactly he must look like, standing in front of his little brother wearing an ancient skirt and _blouse_. Suddenly it’s not as funny as he originally thought it would be.

 “Uh, it’s—it’s a joke, y’know,” Dean says lamely, hands waving out in a vague gesture.

Sam continues to stare at him for another few minutes before he shakes his head and closes his mouth. “Christ, Dean.” 

The slight humor in Sam’s voice thankfully breaks the tension and Dean’s shoulders slump with a relief. Yeah, he knew it was funny. “Found this in an old box in one of the closets. Didn’t know the Men of Letters were such a kinky bunch.” He waggles his eyebrows exaggeratedly for emphasis and gives the skeeviest smirk he can manage.

Sam chuckles and rolls his eyes, “You know, it just as easily could have belonged to a _woman_ , you ever thought of that?”

Dean averts his eyes and shrugs noncommittally. He knows Sam doesn’t mean anything by it, but the fact that he thought of crossdressing old farts instead of, well, a _woman_ wearing this thing kids of makes him feel weird. 

The shift in Dean’s mood must be obvious because Sam’s smile changes to something smooth and easy and he throws his hands up. “Well, I can honestly say you’ve never looked better, Dean.”

“Shut up,” Dean says with more fondness than malice.

Sam shakes his head and crowds closer into Dean’s space to grab his arm and give him an exaggerated leer. “No, no, honest. You look _peachy keen_.” 

Dean snorts. “Whatever, Fonzie.”

Sam’s laugh makes Dean crack a lopsided grin. It’s been so long since Sam’s smiled like that. Dean _knew_ this was an awesome prank.

It’s only then that Dean realizes how close Sam is and he’s inadvertently caging him against the solid oak table. He’s close enough for Dean to smell the spring time-smelling shampoo he uses in his ludicrous hair and see the the faint scar above his lip. The hand on his arm brushes up to clutch shoulder gently.

“Uh.”

Dean blinks and pulls back ( _when did he get so close?_ ), putting space between him and Sam. Sam’s hand on his arm falls away but stays poised in the air, as if it were frozen in time. Dean’s face feels hot and his chest tight. The hem of the skirt brushing against his bare legs feels like sandpaper against his skin.

When he looks up, Sam is frozen in place, hand still raised from where he’d meant to—Dean isn’t sure. He doesn’t want to know.

“Hilarious, Sam,” Dean succeeds in choking out after his throat finally unclenches. 

Sam stands shocked for a few seconds more before blinking and reanimating. His hand drops to his side and the rest of the tensions shatters with it. His whole body sags like his strings have been cut and he looks back over his shoulder to where his laptop sits abandoned. “I should probably get back to researching.” 

Dean nods, relief dissipating the tautness in his shoulders. It’s like the weird moment never happened. Well, despite Dean still being in a skirt. “Yeah! Yeah, you, uh, you do that. I have to go clean the guns anyway.”

Dean’s already cleaned the guns, but he does them again anyway just to not seem like a liar.

____________

“If you get any closer to the page you’re going to merge with it, boy.”

Kevin doesn’t even flinch from where he has his nose buried in one of those ancient-looking, dust-covered books from the library. Dean wonders distantly if immunity to book dust is an inherent geek trait. “I think I’m on to something,” Kevin answers simply, a hint of exasperation in his voice. Dean rolls his eyes and makes sure to bump Kevin’s chair on his way to the kitchen. 

Sam’s drinking a glass of water when he gets there, and it’s obvious he’s been working out by the sweatpants and the way his tank top is soaked around the collar. Dean pointedly doesn’t look at the glistening beads of sweat on Sam’s neck when he says, “You’re up early, Rocky.”

Sam shakes his head and flings sweat everywhere. Dean opens his mouth to chastise him but Sam steamrolls him. “I could say the same for you. It’s 10 AM, you shouldn’t be up for another three hours.”

Dean snorts and steals the pitcher before Sam can pour himself another glass. “I’m thinking we should go find ourselves a hunt,” he says as he pours himself a drink in his favorite mug. He’s not really thirsty, but it wouldn’t look good to spite Sam without actually doing something with it. “I’m starting to get cabin fever, and watching Kevin go through books like candy makes me want to bash my head against the wall.”

Sam’s laugh is free and easy, so rare to hear that Dean doesn’t even protest when Sam snatches his mug and downs it in one gulp. “All right, I can understand that. I’m starting to get a little antsy myself. I’ll search for a job after I take a quick shower.”  
Dean nods and wrinkles his nose, debates between saying a subtle _I wasn’t going to say anything but_ , dude– or a more direct _Please do, you stink to high heaven, man_ when Sam gets a Look in his eyes that has Dean’s witty comment dying on his lips.

It’s an appraising look, half concern and half caution, like he wants to say something but is trying to figure out a way to tell Dean without upsetting him. It’s the same Look he gets before he forces them to have a Serious Talk. The same look that precedes things like I got accepted into Stanford, Dean and I don’t know if I can trust you.

Dean tenses up instantly. He knows what Sam is going to say. Sam is going to bring up the big, skirt-wearing elephant in the room, because for all they’ve pretended until now it wasn’t a _thing_ it was, in fact, a _thing_. If there’s one thing Sam is good at, it’s bringing up _things_ Dean doesn’t want to be _things_.

Goddammit, Dean hates _things_.

Before Sam can get a word out, Dean’s grabbing his mug out of Sam’s slack hand and frowning at it exaggeratedly. “You got your sweaty lips all over my mug, gross. Before you take a shower, wash this out. I’ve gotta go on a grocery run.”

Dean dumps the mug in the sink and half-jogs out of the kitchen. If Sam calls after him, his words are drowned out by the rattling of ceramic on steel.

____________

Sam finds them a hunt in South Portland, Maine. Local news reports strange happenings at a popular make-out spot at the edge of town, ranging from chill winds out of nowhere and vandalized cars, the whole nine.

It’s a pretty open and shut case (vengeful spirit much?) but Sam insists they should hit the library to see what they can dig up any history on the property first anyway. Dean manages to convince him to let him go on a food run while Sam sits buried up to the elbows in archives ( _“Don’t think I don’t know you’re just trying to get out doing actual work, Dean.”_ ) so he dips out and visits a quaint little diner where the grey-haired owner gives him a slice of apple pie on the house for a wink and a smile.

The burger run only manages to kill half an hour, which means there’s probably two hours left of Sam’s research-a-thon. Deciding it’s best to avoid that at any cost, Dean starts walking while he eats, heading in no particular direction to no particular destination. To keep the guilt of ditching work at bay, he half-heartedly goes over the facts he knows about the case while he walks.

Despite not giving 100%–or even 40%, really—to the specifics of the case, when Dean finally snaps his head up he’s in an unfamiliar part of town. None of the buildings look familiar and the street is considerably less lively. Cursing, he juggles the bag of now cold burgers in his arm and fumbles for his phone. Sam’s going to be pissed.

That’s when he realizes he’s standing in front of a modest shop window filled with stark white mannequins sporting crisp-looking dresses. The shop sign reads Sunset Boulevard and the interior looks like something straight out of Leave it to Beaver or I Love Lucy, except splashed with color instead of the black and white grainy filter of a motel TV.

Further into the shop are racks of colorful clothes and mannequins draped in various 1950s fashion. There’s a “Guys” sign over a display of slacks and button downs on one end and a “Dolls” sign over a display of brightly colored poodle skirts and pencil skirts on the other. Posters align the walls with various classic imagery: a group of girls in poodle skirts of varying colors and matching high ponytails laughing, greasers sitting on a candy apple red model T at a drive-in, and at the center a smiling woman stirring a pot on a stove while her husband kisses her cheek. Dean cracks a lopsided grin at the corniness of it all.

As he turns to leave, he spots it: an almost exact replica of the old top and skirt from the bunker, right down to the mossy green color of the skirt with the thin black belt high around the waist. This one is in much better condition, probably because it isn’t actually vintage, and looks almost like it belongs in a movie rather than a tiny little shop in South Portland, Maine.

It’s probably not fair to, or even rational to, but he can’t help but compare it further to the ancient one back home. The skirt is shorter and soft looking, and he imagines what it would feel like brushing against his legs. The shirt’s high neck collar has little silver studs on in, nothing like the stitched lines of the shirt collar at home. The whole shirt’s just way better, really. The shoulders seem wider, like they wouldn’t stretch and pull uncomfortably against the breadth of Dean’s shoulders like the other one did. It looks thicker, though, like if Sam grabbed his shoulder again he wouldn’t be able to feel the full searing warmth of his hand like before. It’s kind of funny to think about, Dean apparently dressing up unwittingly like a some sort of retro housewife. He tries picturing himself cooking and cleaning and waiting for Sam to come home so he can prepare him a big meal and ask him about his day. Going to sleep in separate beds to preserve modesty, but kissing sweet and PG-13 anyway.

“Can I help you with something, sir?” A blue-haired woman wearing a Rosie the Riveter shirt asks from the open door. Billy Vaugn’s _Sail Along Silvery Moon_ wafts softly out of the shop behind her.

Dean jumps about ten feet in the air and almost drops the sack of definitely cold burgers on the ground. “Uh—,” he can feel the blush creeping up his neck and the familiar prickly feeling of shame under his skin. It feels like he’s just been caught perving in the women’s lingerie section. This woman probably thinks he’s some sort of kinky freak. “Uh, no! No, I was just—”

“Dean!”

Dean whirls around to face a pissed off Sam angrily stomping his way. Billy Vaughn croons “ _Two blue hearts will be lighter_ ” before cutting off completely, probably because the woman from the shop would rather stay inside than confront a peeping Tom and a stampeding Sasquatch. 

“What the hell are you doing here?” Sam huffs when he finally reaches Dean, standing up to his whole height as he glares down at him from on-high. Dean would probably make fun of him for it if he wasn’t still shaking.

“What—how did you—?”

“GPS,” Sam snaps irritably. “You were supposed to be back over an hour ago.”

Dean is blinking rapidly and trying to stutter out the best lie he can think of at the moment when he realizes Sam isn’t trying to desecrate him with his eyes anymore.

Sam’s standing stock still, shoulders still tense but hands uncurled from fists. The first thought in Dean’s mind is that he should take advantage of this unexpected leeway and jet for the car where he can turn the music up loud and drown out the sound of Sam chewing his ass out. The second is the irrational thought that Sam is struck still because he’s hurt. Dean doesn’t quite get to the third thought because when he realizes what Sam’s actually doing his mind completely shuts down.

Sam is staring at the mannequin with the outfit, the one that looks identical to the one Dean had worn at the bunker, the one Dean had just been staring at while he fantasized about playing house with his little brother. The blush from before comes back in full force, and Dean feels bile rising in his throat at Sam’s slightly blown expression.

It takes a few tries, but eventually Dean works around the lump in his throat. “So, did you find anything?”

It’s a weak attempt at distraction, but it succeeds in snapping Sam’s attention away from the outfit. Unfortunately, that puts Dean smack dab in the line of Sam’s concerned, knowing gaze. “Dean—”

“Nah, let’s talk about it on the way back to the motel. Wait, scratch that, let’s go back to that diner and get some more of these burgers. They’re the best damn burgers I’ve tasted in a while. Well, besides mine, of course.” Dean knows he’s rambling, but his heart is doing double time in his chest and he’s pretty sure the words ‘I’m a big sissy freak who thinks about necking his little brother while wearing dresses’ are spelled out in block letters all over his face.

And fuck Sam for knowing Dean better than Dean knows himself, because he sees right through the bullshit he’s trying to sell and gives him an almost pitying look, similar to he ones he gives the snot-covered grieving widow vics during their home interviews. It makes Dean’s stomach roll. “Dean, I—”

Dean shoulders passed Sam and walks towards where he sees the impala parked, pace just this side of too fast to be casual. “C’mon, Sammy, we’re wasting daylight.”

Dean’s heart doesn’t stop pounding even though Sam doesn’t say anything after slipping into the passengers seat. It doesn’t stop pounding all the way from the diner to their motel and Dean’s certain it’s going to smash right out of his chest. He doesn’t eat his burger.

____________

The hunt goes off without a hitch and Dean gets the celebratory shots he envisioned and then some. He drinks too much whiskey and orders too much bar food and Sam rolls his eyes affectionately the whole time. It’s a really good night.

They stay until bar close and by then they’re way too buzzed to even consider the drive back home so it’s back to the motel for another night. Sam falls face-first into his bed when they get there and Dean bangs around as he gets ready for his shower, belting out Ramblin’ Man just to be obnoxious.

“Can you shut the hell up?” Sam groans from the pillow he’s shoved his head under. Dean throws his head back and laughs heartily, giddy and loose from victory and alcohol.

“ _They're always having a good time down on the bayou, Lord_ ,” he belts out even louder as he digs through his duffel for something to change into. “ _Them Delta women think the world of me_.”

Sam groans even louder and whips his head up to glare daggers at Dean. “Jesus _Christ_ , Dean.”

Sam freezes, wide-eyed and mouth open, and Dean only has a split second to think of how funny it is before he realizes Sam’s gawking at the little panties that have fallen out of his duffel.

Fighting the immobilization of panic, Dean snatches them up and shoves them back to the dark corner of his duffel, face beet-red and ears pounding. Fuck, he’d forgotten it was this duffel he—God, what was he _thinking_ —

“I’m taking a shower,” Dean mumbles, his voice sounding harsh and off to his own ears. He tries to rush quickly to the bathroom without looking like he’s running way—which is exactly he’s trying to do.

“Wait,” Sam says a little bit too loud for the silent room, and how did he get up so fast? “ _Dean_.”

Dean halts and wracks his brain for a way out, something to save him from this. “Remember that poltergeist we iced back in Chesapeake? The one terrorizing the window, the chick who thought you were a ?” He says in a easy tone that only barely masks how much he’s trembling. Sam’s got a lot on his face like he knows where this is going and he’s already sick of it. “While you were out back getting us ready to head up, she gave me a pretty sweet solo ‘thank you’.” Dean shrugs with a cocky smirk he knows doesn’t meet his eyes and tries not to flinch when Sam looks back at the duffel.

When Sam turns back around, his face is unreadable. “Dean,” he sighs quietly as he reaches a hand out to touch Dean’s cheek. It’s dark and in the room and they’re standing too close and when did it get like this?

Dean knows about this _thing_ between them. The thing they never talk about or act on but is always there, layered under every reassuring pat on the back and gently stitch of torn skin. The _thing_ that keeps Dean watching his little brother, tracing every worry line and reluctant smile with a heavy heart. The _thing_ that has Sam leaning in close enough for Dean to feel his breath on his lips, close enough to—

“It’s okay,” Sam whispers. “It’s okay, I promise.”

With a jerk, Dean pulls back and nearly smacks his head against the bathroom door. Sam stares at him with startled, open eyes and something else that Dean doesn’t take the time to decode.

“I’m taking a shower,” he says again lamely as he turns around and locks himself inside the bathroom, the tile cold under his ass when he slides down to compose himself.

When he slips out 15 minutes later Sam is pretending to be asleep, back facing Dean’s bed uncharacteristically. Dean slips under his own covers quietly and waits for morning.

____________

Sam’s out talking to a vic on a new hunt, local this time, and Dean’s opted out, citing a bad Thai food as a reason to stay home. Usually, Sam would see right through his lie and would nag him until he relented, but this time he leaves him home alone (Kevin miles away in some random motel, probably masturbating to ancient texts) without incident. Dean should be relieved, but he’s not.

Sam isn’t talking to him.

Okay, Sam’s talking to him, but he’s not talk-talking to him. They talk about things, like the weather and prospective hunts, but they don’t actually _talk_ about things. Sam doesn’t tell him to stop chewing with this mouthful or to leave Kevin alone or to stop using his favorite bowl. It feels like living with a coworker instead of his little brother, and all because of a stupid pair of panties.

The stupid pair of panties Dean’s staring at right now. The stupid pair of panties that don’t exactly match the old skirt and top he found in one of the closet before. The stupid pair of panties he going to fucking where with them anyway.

Because Dean Winchester is going to do this. Goddamn him, he’s going to do this.

Before, it was somehow easier to peg it as just a weird fetish. Millions of creepy perverted mean pushing 50 probably got off to the idea of wearing panties or sporting dresses. During one of his many all-night porn session, Dean had even managed to stumble on a website where men paid women to make them wear panties, to be humiliated and shit. He had never exited out of a tab so fast in his life.

But truthfully, gun to his head, that wasn’t all it was. It hadn’t been all it was since he was 13, staring at the Foxy Brown vintage poster he had gotten for 75 cents at a garage sale, fingers tracing the billowy lines of Pam Grier’s dress as she stared hotly back at him. The feeling of being confused as to whether he wanted to kiss her or _be_ her was still fresh in his mind, terrifying and exciting all at once.

He remembers the day John had found the folded up poster buried in the side of his sock drawer under the hunting knife he kept as back up. The gripping fear had been replaced with red hot shame when he realized that John’s amused smile wasn’t because he knew Dean’s thoughts about the dress, but what he should have—what most boys his age should have—been keeping it for.

It wasn’t until his sophomore year in high school, still a little wet behind the ears but excited enough about girls to dive in anyway, that the feeling came back to latch on to him in the form of Rhonda Hurley’s pretty pink lips and equally pretty pink panties.

By then the old Foxy Brown poster had been lost to a nameless motel somewhere across the U.S., and the old, confusing feeling with it as far as Dean was concerned. Until Rhonda leaned over him from where he lied beneath her on her princess-themed bed, bare breasts soft against his chest, and whispered, “I want you to do something for me,” that he realized he was fucked.

Wearing those panties while he ate her out had been an almost religious experience. He had felt softer, yet stronger than he had in years. The feeling of the silky fabric brushing against his cock and balls as he maneuvered her legs up and apart sent sparks up his spine and undefined thrills through his veins. It was like wearing the little thing had made sex better by making _Dean_ better.

He was grateful when Rhonda didn’t say a word when he moved them to the side to free his cock to fuck her instead of taking them off. He downright wanted to praise her when she only smiled as he stuffed them in his pocket on the way out.

When John had found those, he’d given Dean a lopsided smile equal parts scolding and congratulatory, but what he stood out about that was the _looks_ he’d given him afterwards. Not quite accusatory or disgusted, but confused, like there was something about Dean he couldn’t quite figure out. It made Dean’s skin crawl and drove him up the wall so much he’d ditched those pretty pink panties in a dumpster outside of another nameless motel in Kentucky a week after. 

And now he’s got a new pair, blue and lacey instead of pink and satiny, and he’s going to where them for someone a lot more important than Rhonda Hurlely.

It takes an hour to get ready and he feels stupid the entire time. The panties are kind of itchy against his thighs and the skirt fits a little weirder than he remembers, but he can’t bring himself to look into a mirror to check himself. 

To keep his hands busy, Dean texts Sam _u done?_ to which Sam replies with a quick _yeah. got squat. heading back now._ Dean drops his phone to adjust the cinched belt digging into his abdomen before picking it up with shaky hands and texting _what u want for dinner? ___Dean feels like he’s waiting on a death sentence the entire time until Sam texts back a few seconds later: _pasta?_

Dean nods to himself before dropping the phone on the counter and getting to work.

____________

When the door slams and Sam’s “Hey” echoes the room Dean almost drops his spoon in the pasta sauce. His heart speeds up double time and the _Oh god what the fuck am I doing_ hits tenfold. Dean is suddenly, painfully aware of how _wrong_ this is, how wrong he looks. The sweater is ill-fitted, not designed to stretch across his wide shoulders, and loose and unappealing in the front where Dean doesn’t have breasts to fill it. His figure is all wrong, flat instead of curvy, and not even the high waist gives an illusion to otherwise. He’s bulky where he should be slim and chubby where he should be full and everything about it is just _wrong_. He’s a man in a dress, for fuck’s sake. He’s a man in a dress waiting for his little brother to come home and—

The sound of Sam’s sharp exhale startles Dean out of his panicked brooding and he only barely manages to save the spoon from really dropping into the sauce this time.

Dean turns to where Sam is standing in the doorway, mouth fallen open in an ‘o’ and eyes wide. It’s a testament to how fucked up all of this is—how fucked up _Dean_ is—that his first thought is how much Sam looks like the handsome working husband from the 1950s shop poster in his crisp blue suit.

It takes all of Dean’s willpower not to just bolt. It had been easy the first time to play it off as a joke. Fuck, it _had_ been a joke, before it spiraled into something much bigger and all-consuming. Now that he’s here again, cooking Sam’s favorite foods and waiting for him to get home like one of the smiling broads from a Good Housekeeping cover, there is no way to get out of this without broadcasting how obviously into it he is.

Instead, Dean turns back to the bubbling sauce on the stove and says in the most casual tone he can muster, “Hey, Sammy. How was your day?”

A tense, loaded silence follows, only penetrated by the slight clank of the wooden spoon against the pan as Dean determinedly continues cooking. He’s pretty sure he can’t breathe.

Suddenly the hair on the back of his neck is standing up as Sam stands closely behind him, chest pressed casually to Dean’s back as he leans one hand on the counter. Dean’s heart is beating so loud there’s no way Sam can’t hear it.

Dean sees a flash of out of the corner of his eyes where Sam is leaning over. “You cook all of this for me, Dean?”

Dean blinks owlishly, remembering that cooking _is_ what he’s doing right now. ”Uh,” Dean stutters out dumbly. Sam presses minutely closer and Dean feels like his skin is on fire. “I—yeah. I just, yeah.”

Dean can feel Sam’s eyes on him as leans over to check the noodles. He should probably check on the roasted asparagus in the oven, but that would mean crowding back into Sam’s space, and the thought is too damning and too thrilling for Dean to risk it.

Sam places his hands on Dean’s waist, a little too high up because of the cinched belt, and Dean swallows down an embarrassing noise. He can feel warmth pooling low in his belly, the thrill of anticipation up his spine. 

“What all we got here, hmm?” Sam says, and he’s pressed so close Dean can feel the vibrations of his words against his back.

He lifts the lid off the steaming noodles with shaking fingers. “Uh, pasta, like you wanted. Got some baked asparagus in the oven and little stewed cabbage. I was gonna make some salad, too, the kind with the weird cube stuff you like. There’s some ice cream left, so I was thinking we could have sweet potato pie for dessert, but I don’t know if you’re still on that weird “no sweets” health kick. I mean, I’ll make it anyway. Whether you’re crazy and only eat no fat diet kale cakes or some shit like that for dessert, I’m actually _sane_ —”

Dean’s rambling is cut off with a sharp gasp as Sam presses impossibly closer, the outline of his dick pressing against his ass. Sam hums, the vibrations sending pleasant shivers through Dean’s body. “Everything smells amazing, Dean. This is just what I need after what happened today. You always know how to take such good care of me, don’t you?”

It’s a little mortifying how fucking happy that makes him, how hot and needy Sam praising him gets him. It’s a good thing he can’t see Sam’s face right now. If there’s half as much affection in his eyes as there is in his tone, Dean might do or say something embarrassing. “What happened today?” Dean asks in a quiet voice, if only to steer the conversation away from himself.

Dean feels Sam shrug against his back. “It’s kind of a long story. You wanna join me in the other room?”

Dean nods mutely and Sam waits patiently while he turns the dishes on low. The walk from the kitchen to the living area feels a mile long with Sam’s hand relaxed and possessive on the small of his back the whole time.

Sam drops heavily on the couch (Dean’s idea to move one in, because fuck if he’ll be sitting on those hard wooden chairs all the time) with a sigh closes his eyes. Dean stands awkwardly in front of him, eyes tracing the tired lines around his eyes. A distressed voice in his head tells him he picked the wrong time to do this, that Sam is probably too tired after going it alone today, and there’s no way he’ll be able to get the courage to try this again. 

Then Sam opens his eyes and pins him with a dark, hungry look, and all thought is wiped from Dean’s mind. It’s the only reason he moves when Sam says a soft, firm “C’mere,” and pats his lap invitingly.

Dean isn’t small, not by any stretch of the word, but sitting in Sam’s lap, one of his giant paws on his thigh while the other rubs absently at his back, he feels impossibly small. The fact shouldn’t get him as hard as he does, but he’s beyond pretending he’s not fucked up.

“The vic was kind of an ass,” Sam starts, and Dean’s so dazed it takes him a few seconds to realize that Sam’s talking about his day. “I mean, the guy’s been through a lot—it’s not everyday that your furniture starts rearranging itself into intricate structures—but he made it abundantly clear he wasn’t interested in my help.”

Sam’s tone is light and amused, betraying the sensual drag of his hand higher and higher up Dean’s thigh. Despite the subject matter, and the fact that they’re brothers and Dean’s a man in a dress, it feels like they’re almost a normal husband and wife. LIke there’s no demons or angels or heaven or hell and Sam’s a lawyer, tired after a long day at the office, and Dean’s his obedient little wife with dinner and a smile ready when he gets home. Dean breathes out shakily. “Fucking hicks, man.”

Sam laughs deep and genuine and Dean finds himself smiling in response. “I actually thought the same thing, especially when he subtly let me know he was technically allowed to shoot me if I refused to leave his property.”

There’s a lot of things Dean could say to that, some more colorful than others, but it’s like the words wont’ come out. “That’s okay, though, because I came home to a wonderful dinner prepared by my—my Dean.”

There’s heat crawling up the back of Dean’s neck as he forces an overly-cocky smirk. “I’m a double threat, Sammy: Demon hunter slash housewife.”

The last word comes out strained and quiet, like saying it out loud somehow makes this whole situation that much more real. The feeling of shame and doubt comes back with a vengeance and Dean seriously starts to weigh the consequences of standing up right now and telling Sam this was all a joke.

As if sensing Dean’s thoughts, Sam’s hand tightens on his thigh while his other hand grips Dean’s chin to bring him closer. Sam’s eyes are the color of lit coal as the bore into Dean. “Yeah, you’re a good little housewife. _My_ good little housewife.”

Dean shudders almost violently and his eyes slip closed, not able to take the feeling of Sam’s hands on him and his breath against his face and his eyes filled with want and his dirty-wrong words. It’s like Sam-overload, and Dean’s sure if he doesn’t block out one of them he’s going to tear apart at the seams.

Sam’s lips pressing against his is unexpected, but Dean melts into it with ease after a few stunned seconds. Sam’s lips are soft and slightly chapped at the corners, the kiss chaste but firm. When Sam tongues at Dean’s lips, he’s not asking, he’s taking, and Dean moans hot and needy as he opens up and gives all he has.

It’s hot and wet and just this side of desperate to suck the air right out of him. It feels like Sam’s hands are everywhere, pawing at his back and his thighs and his hair and neck. Dean’s hands are laced in Sam’s ridiculous hair and he needs so much _more_ but the stupid fucking skirt is constricting his legs, keeping him from turning to straddle Sam and rut against him like a bitch in heat.

Dean pulls back with a frustrated grunt and fumbles with the belt around his waist in a rush to rip it off. Sam grabs his hands in a strong grip and pulls them away to quick it almost hurts, startling Dean into stilling. “Shit, no, just...keep it on. Let me—”

Sam pushes at Dean gently until he gets the message and rolls off his lap and flops on the couch. Dean doesn’t even have a moment to wonder (worry) what Sam is doing before Sam is pushing him face down into the couch and yanking up his hips. Dean’s hand flail out to steady himself so he doesn’t end up face-planting.

Long, calloused fingers lift his skirt up and over his hips. Dean shivers and presses his burning face against the cushion. He had almost forgotten about this part, the extra mile he’d gone to pull this thing together. He feels hyperaware of everything, 

“Jesus, Dean,” Sam whispers behind him, sounding almost reverent as he runs a hand up panty-covered ass. Dean’s thighs are stiff as Sam runs lips over the fabric, hands roaming over the slip of exposed skin where the panties ends and the nylon stockings begin.

“Fuck,” Dean whispers shakily, face still pressed into the cushion. Sam’s murmuring something against the swell of his ass, and Dean strains not to hear, afraid that whatever it is might send him over the edge right this second.

Sam tugs the panties down to Dean’s mid-thigh and Dean’s hard dick slips out and bobs between his legs. He runs his tongue over the crack of Dean’s ass and brings to huge hands up to knead at the flesh of his cheeks slowly. Dean jerks shakily and strains back to get more of it, knees instinctively trying to part for more purchase. He’s trapped with the panties around his thighs, can’t move back for more, can only get it if Sam decides to give it to him, and fuck if that doesn’t make Dean _want_.

When Sam’s tongue finally breeches the ring of his ass, Dean has to bite down hard on his lip to keep down an embarrassing whimper. Sam moans heartily behind him, like going down on his macho big brother is the best damn thing he’s ever done. Dean feels wet and open, like he really is a fucking girl, a horny little housewife who’s going to be road hard and put away wet.

“Sam,” he whisper-groans, not able to conceal the fucked-out want in his voice. “Sam.”

Sam groans what could be his name where his buried between Dean’s cheeks, hands massaging the slightly chubby skin of his inner thighs, knuckles occasionally brushing his twitching erection and making Dean grunt helplessly. 

When Sam pulls back with an obscenely wet sound Dean can’t stop a desperate keen from slipping out. Sam murmurs nonsense soothing words and rubs the small of Dean’s back quickly before he stands up. “Stay. I’ll be right back.”

Dean wants to balk indignantly, get up right now and start calling the shots here, goddammit. He’s not, though, and he doesn’t. He nods mutely and stays resting on his forearms with his ass high in the air, panties around his thighs and hole wet and open and waiting. Waiting for Sam. _God_.

Sam rips Dean out of his stewing thoughts by gently nudging him on the shoulder. He whips his head up to where Sam is towering over him—the boy’s fucking _huge_ , fucking huge all over—and the look in his eye makes him feel hot all over.

“Come here,” Sam whispers as he sits down on the couch again, and Dean scrambles to pull his panties out of the way to do just that, if only to keep his ass off display. Even though Sam is the one that got him that way. Even though they’re about to do way more, if the bottle of lotion in Sam’s hand is any indication.

He settles in Sam’s lap facing him this time, skirt still hiked up around his hips to give him room to move, panties hanging off one thigh in his haste. Sam laughs breathlessly as he grips his hips, and the sound makes Dean feel more happy than embarrassed.

They’re kissing again, just as heated as the first time but with the promise of what’s to come lacing every glide. Dean’s not sure how long they stay like that, kissing wet and desperate, Dean bare bellow the waist and grinding against the rough fabric of Sam’s suit pants, but when he pulls back with a gasp as Sam’s prodding a lotion-slicked finger at his rim it feels like his first time breathing air.

Dean’s still loosened up from before, though the push still burns a little. It’s been a while since he’s been opened up, whether by himself or with someone else, but this time feels different, easier. Maybe it’s because Sam took the time to open him up with his tongue. Maybe it’s just because it’s Sam.

By the time Sam gets three fingers inside of him he’s shaking. His fingers are clutching Sam’s broad shoulders in twin white-knuckled grips and he’s worried his lip so much it’s a surprise he hasn’t cut clean through it. “Fuck, Dean,” Sam pants as Dean works himself open on his fingers. “Gotta get in you, fuck.”

Dean couldn’t pull himself away from Sam right now even if he wanted, but he needs to see Sam hard and wanting this as bad as he is. He leans back just enough to allow Sam to tug off his belt and undo his pants and pull out his hard (fucking _huge_ ) dick, angry red at the tip and standing proud. 

It’s makes an obscene picture: Sam’s sitting back in his pressed blue suit with his big brother wearing a skirt in his lap, his cock out and iron-hard. Dean wonders what it would taste like to run his tongue over the shiny-red tip of his little brother’s cock, what it might feel like to suck him down far enough to press his nose in the curly dark hair at the base. 

Later, he promises himself, because after today there might actually be a chance for later. He watches Sam slick himself up with lotion with hungry eyes, and after a few seconds of awkward fumbling and nervous laughter, Dean finally sinks down onto Sam’s cock with a guttural moan.

It really has been a while since he’s done this, but he just needs so bad he doesn’t even stop to adjust, just works himself up and down on Sam’s cock with abandon. Sam moans deep and rough underneath him, his hands gripping Dean’s hips with bruising grips. Dean’s cock bobs obscenely between them and their panting echoes in the otherwise silent room.

“God, yeah, fuck, you want it so bad,” Sam sounds awed and lusty under him. Dean has the irrational urge to push the sweaty locks sticking to his temples out of the way, but he’s certain if he let’s go of Sam’s shoulders he’ll end up toppling back from the force of his thrusts.

He wishes he could see them right now. He’s wet and sloppy where he’s fucking himself up and down on his little brother’s cock, skirt hiked up around his hips, one stocking sliding down his thigh, and his little blue panties laying abandoned around one thigh. It’s dirty and bad and wrong and so, so good. 

His orgasm hits him like a freight train, scorching and consuming. A high, keening sound tears from his throat as he comes between them, shuddering and completely untouched. He’s still dazed when Sam presses their bodies together enough to fuck up up into him with renewed intensity. 

Sam comes inside of him with a loud, choked groan. Dean catalogues every whimper and gasp as he goes up and comes back down, wanting to solidify it in his memory and keep it forever.

When they’ve both come down, breath evening out to faint huffs, Sam nudges him gently in the side with a finger. Dean grunts gracelessly in response with his nose buried in the crook Sam’s neck. “Dean, I think you should check on the food.”

Dean pulls back enough to let Sam see him roll his eyes exaggeratedly before he unceremoniously ambles off his lap and back on coltish legs. The panties held on one leg fall to the ground and he and Sam stare at it silently.

“Mmm,” Sam hums, almost contemplating. He watches Sam tuck himself back inside his pants with way more grace than someone who just had an orgasm should have. When Sam beckons Dean closer with a hand, he doesn’t even think about disobeying.

Sam gets up and bends down to tug at the discarded panties at Dean’s feet and maneuvers him over until he can pull the panties back up around Dean’s hips. Dean doesn’t do much except stay still while Sam smooths his skirt back down, Sam making him presentable after making a mess of him. He doesn’t even protest when he feels Sam’s come leaking out of his ass and dirtying up his panties, just feels his cock twitch weakly in response.

Sam’s hands rest warm and anchoring on his hips and his cat eyes bore into Dean’s with a level of affection and intensity that makes him want to turn his face away. He wants to kiss Sam again. He wants to bury his fingers in Sam’s ridiculous long hair and kiss him when he comes home for work. He wants to have food ready when Sam gets hungry and massage his shoulders when he gets tense. He wants to lie down and let Sam make a mess of his panties. He wants so much of what he knows they can never have and it’s so stupid this yearning has to come from wearing a goddamn skirt.

Sam, who always knows when Dean gets too caught up in his cobweb thoughts and knows just how to pull him back when he’s teetering on the edge bats away the darkness of Dean’s thoughts with a long, slow kiss. And fuck, Dean’s never going to get tired of kissing Sam.

“Dinner, Dean,” Sam murmurs against his lips, and it sounds like so much more.

“Yeah,” Dean murmurs back but he doesn’t move, just presses closer to the warm embrace of Sam’s arms.

**Author's Note:**

> This fic is a fill for this [spnkink-meme prompt](http://spnkink-meme.livejournal.com/78445.html?thread=28980077#t28980077): "Dean somehow winds up with a 1950s housewife dress and apron and decides to put it on in the bunker to crack a joke and mess with Sam. Shockingly enough, Dean finds out that he actually likes putting it and the facade that goes along with it on: He's no longer Dean the big hunter with all this responsibility and lies to keep, he's a traditional housewife who only has to worry about cooking and cleaning and pleasing her man. Sam realizes how much Dean likes and needs this and decides to subtly play along as the big man, head of the household type to complete Dean's perfect little fantasy."
> 
> I hope the prompter enjoyed this!
> 
> If you're interested in what I envisioned for the outfit: [link](https://24.media.tumblr.com/74bbe693580ed1fafb5a7a57d3fa1828/tumblr_n0t449geKJ1qzqx3bo1_400.jpg)


End file.
